(19)
(11) EP 0 199 413 A3

(12) EUROPEAN PATENT APPLICATION

(88) Date of publication A3:
06.05.1987 Bulletin 1987/19

(43) Date of publication A2:
29.10.1986 Bulletin 1986/44

(21) Application number: 86200639

(22) Date of filing: 15.04.1986
(84) Designated Contracting States:
AT BE CH DE FR GB IT LI LU NL SE

(30) Priority: 16.04.1985 GB 8509746

(71) Applicant: SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ B.V.
 ()

(72) Inventors:
  • Verbrugge, Pieter Adriaan
     ()
  • de Waal, Jannetje
     ()
  • Sopher, David William
     ()

   


(54) Process for preparing azetidine derivatives and novel intermediates therein


(57) Process for the preparation of a compound of formula or a salt thereof

wherein R, represents a hydrogen atom or a group of formula R2SO2 or phenyl-CH(R3)-wherein R2 represents a phenyl, tolyl or C1-4 alkyl group and R3 represents a hydrogen atom or a phenyl or C 1.4 alkyl group, which process comprises contacting nickel in an oxidation state of at least 3 with a 3-hydroxymethyl azetidine derivative of formula

wherein R4 represents a group of formula R2SO2 or phenyl-CH(R3)-and R5 represents a hydrogen atom or a hydroxymethyl group or a group of formula COOH or a salt thereof, followed, where R5 is not a hydrogen atom, by the decarboxylation of the compound of the 3,3-dicarboxylic intermediate product or a salt thereof and. if desired to produce a compound in which R. represents a hydrogen atom, by deprotection of the N-atom. Also. novel N-substituted azetidine carboxylate derivatives of the formula

wherein X represents a group CH2OH or COOY where Y represents a hydrogen or an alkali or alkaline earth metal atom.





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